PL219017B1 - Pochodna benzazepiny, zawierająca ją kompozycja oraz jej zastosowanie - Google Patents
Pochodna benzazepiny, zawierająca ją kompozycja oraz jej zastosowanieInfo
- Publication number
- PL219017B1 PL219017B1 PL391779A PL39177903A PL219017B1 PL 219017 B1 PL219017 B1 PL 219017B1 PL 391779 A PL391779 A PL 391779A PL 39177903 A PL39177903 A PL 39177903A PL 219017 B1 PL219017 B1 PL 219017B1
- Authority
- PL
- Poland
- Prior art keywords
- benzazepine
- tetrahydro
- methyl
- methoxy
- bromo
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 180
- 239000000203 mixture Substances 0.000 title description 123
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 239000012453 solvate Substances 0.000 claims abstract description 26
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 43
- 150000002367 halogens Chemical group 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 37
- 208000008589 Obesity Diseases 0.000 claims description 35
- 235000020824 obesity Nutrition 0.000 claims description 34
- 239000003814 drug Substances 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 241000124008 Mammalia Species 0.000 claims description 17
- -1 methoxy, ethoxy, n-propoxy, isopropoxy Chemical group 0.000 claims description 17
- 150000004677 hydrates Chemical class 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 235000012631 food intake Nutrition 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 230000037406 food intake Effects 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- KTCVEIAEKPSBCJ-UHFFFAOYSA-N 7,8-dichloro-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC(Cl)=C(Cl)C=C12 KTCVEIAEKPSBCJ-UHFFFAOYSA-N 0.000 claims description 7
- KRBZRTWDEJCQIL-UHFFFAOYSA-N 7-bromo-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC=C(Br)C=C12 KRBZRTWDEJCQIL-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 7
- 235000019786 weight gain Nutrition 0.000 claims description 7
- PIFUPUQFKHPAJN-UHFFFAOYSA-N (7-bromo-8-methoxy-2,3,4,5-tetrahydro-1h-3-benzazepin-5-yl)methanol Chemical compound C1CNCC(CO)C2=C1C=C(OC)C(Br)=C2 PIFUPUQFKHPAJN-UHFFFAOYSA-N 0.000 claims description 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- HQQAIJWQKAFMGF-UHFFFAOYSA-N 7-bromo-8-methoxy-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OC)C(Br)=C2 HQQAIJWQKAFMGF-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- RYYXCFYKJMRFPZ-UHFFFAOYSA-N 5-ethyl-7-iodo-8-methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CCC1CNCCC2=CC(OC)=C(I)C=C12 RYYXCFYKJMRFPZ-UHFFFAOYSA-N 0.000 claims description 5
- ZSPRCURTNKXTKN-UHFFFAOYSA-N 7-bromo-2,5-dimethyl-8-prop-2-enoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNC(C)CC2=CC(OCC=C)=C(Br)C=C21 ZSPRCURTNKXTKN-UHFFFAOYSA-N 0.000 claims description 5
- CJNIKSUHKLMLAY-UHFFFAOYSA-N 7-bromo-5-cyclopropyl-8-methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1=2C=C(Br)C(OC)=CC=2CCNCC1C1CC1 CJNIKSUHKLMLAY-UHFFFAOYSA-N 0.000 claims description 5
- UWFSZQMKPCCKFT-UHFFFAOYSA-N 7-bromo-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepin-8-ol Chemical compound CC1CNCCC2=CC(O)=C(Br)C=C12 UWFSZQMKPCCKFT-UHFFFAOYSA-N 0.000 claims description 5
- BNEIDDXVFTVOOR-UHFFFAOYSA-N 7-bromo-5-methyl-8-phenylmethoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound BrC=1C=C2C(C)CNCCC2=CC=1OCC1=CC=CC=C1 BNEIDDXVFTVOOR-UHFFFAOYSA-N 0.000 claims description 5
- IYWYWVMPIJVOBD-UHFFFAOYSA-N 7-bromo-5-methyl-8-prop-2-enoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC(OCC=C)=C(Br)C=C12 IYWYWVMPIJVOBD-UHFFFAOYSA-N 0.000 claims description 5
- OKANWZMGTYYNOW-UHFFFAOYSA-N 7-bromo-5-methyl-8-propan-2-yloxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OC(C)C)C(Br)=C2 OKANWZMGTYYNOW-UHFFFAOYSA-N 0.000 claims description 5
- YJMJIRPWYQUXFC-UHFFFAOYSA-N 7-bromo-5-propan-2-yl-2,3,4,5-tetrahydro-1h-3-benzazepin-8-ol Chemical compound CC(C)C1CNCCC2=CC(O)=C(Br)C=C12 YJMJIRPWYQUXFC-UHFFFAOYSA-N 0.000 claims description 5
- CABPILKLTHGNHC-UHFFFAOYSA-N 7-bromo-5-propan-2-yl-8-prop-2-enoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC(C)C1CNCCC2=CC(OCC=C)=C(Br)C=C12 CABPILKLTHGNHC-UHFFFAOYSA-N 0.000 claims description 5
- LQGCCOADXMPGTL-UHFFFAOYSA-N 7-bromo-8-ethoxy-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OCC)C(Br)=C2 LQGCCOADXMPGTL-UHFFFAOYSA-N 0.000 claims description 5
- XHRJDETZSGXGJN-UHFFFAOYSA-N 7-bromo-8-methoxy-2,5-dimethyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1C(C)NCC(C)C2=C1C=C(OC)C(Br)=C2 XHRJDETZSGXGJN-UHFFFAOYSA-N 0.000 claims description 5
- TZUDPSHMYVSTRR-UHFFFAOYSA-N 7-bromo-8-methoxy-3,5-dimethyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1CN(C)CC(C)C2=C1C=C(OC)C(Br)=C2 TZUDPSHMYVSTRR-UHFFFAOYSA-N 0.000 claims description 5
- IHRBUEKNYVJQIC-UHFFFAOYSA-N 7-bromo-8-methoxy-5-propan-2-yl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C(C)C)C2=C1C=C(OC)C(Br)=C2 IHRBUEKNYVJQIC-UHFFFAOYSA-N 0.000 claims description 5
- KVGYVFPNKGJTTP-UHFFFAOYSA-N 7-chloro-2,3,4,5-tetrahydro-1h-3-benzazepin-5-ol Chemical compound OC1CNCCC2=CC=C(Cl)C=C12 KVGYVFPNKGJTTP-UHFFFAOYSA-N 0.000 claims description 5
- BPLNPUPEOXRWMZ-UHFFFAOYSA-N 7-chloro-3,5-dimethyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound CC1CN(C)CCC2=CC=C(Cl)C=C12 BPLNPUPEOXRWMZ-UHFFFAOYSA-N 0.000 claims description 5
- OSCDHVCJRHGBTH-UHFFFAOYSA-N 7-chloro-5-methyl-8-prop-2-enoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC(OCC=C)=C(Cl)C=C12 OSCDHVCJRHGBTH-UHFFFAOYSA-N 0.000 claims description 5
- CKXNNAQKSQRYNX-UHFFFAOYSA-N 7-chloro-8-(2-fluorophenyl)-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound ClC=1C=C2C(C)CNCCC2=CC=1C1=CC=CC=C1F CKXNNAQKSQRYNX-UHFFFAOYSA-N 0.000 claims description 5
- TXVNTTRQUFIPMP-UHFFFAOYSA-N 7-fluoro-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC=C(F)C=C12 TXVNTTRQUFIPMP-UHFFFAOYSA-N 0.000 claims description 5
- DCHHWZZHLKXNCB-UHFFFAOYSA-N 7-iodo-5-methyl-8-(trifluoromethoxy)-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC(OC(F)(F)F)=C(I)C=C12 DCHHWZZHLKXNCB-UHFFFAOYSA-N 0.000 claims description 5
- SONAPYLGIVLEEN-UHFFFAOYSA-N 7-iodo-5-methyl-8-prop-2-enoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC(OCC=C)=C(I)C=C12 SONAPYLGIVLEEN-UHFFFAOYSA-N 0.000 claims description 5
- RRUVWNUSSPWKJJ-UHFFFAOYSA-N 7-iodo-8-methoxy-5-methyl-3-propyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound CC1CN(CCC)CCC2=CC(OC)=C(I)C=C21 RRUVWNUSSPWKJJ-UHFFFAOYSA-N 0.000 claims description 5
- BOQDOEZEZODMKK-UHFFFAOYSA-N 8-methoxy-5-methyl-7-thiophen-2-yl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound COC1=CC=2CCNCC(C)C=2C=C1C1=CC=CS1 BOQDOEZEZODMKK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- GBYLNYMTYZRQLE-UHFFFAOYSA-N 5-methyl-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC=C(C(F)(F)F)C=C12 GBYLNYMTYZRQLE-UHFFFAOYSA-N 0.000 claims description 4
- ZVWYXVHPZNQTGP-UHFFFAOYSA-N 7-(2-chlorophenyl)-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1=C2C(C)CNCCC2=CC=C1C1=CC=CC=C1Cl ZVWYXVHPZNQTGP-UHFFFAOYSA-N 0.000 claims description 4
- QSLHEIFNJPYBLS-UHFFFAOYSA-N 7-bromo-5-ethyl-8-methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CCC1CNCCC2=CC(OC)=C(Br)C=C12 QSLHEIFNJPYBLS-UHFFFAOYSA-N 0.000 claims description 4
- JHQHEPFCSFITQT-UHFFFAOYSA-N 7-bromo-8-methoxy-5-(methoxymethyl)-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound COCC1CNCCC2=CC(OC)=C(Br)C=C12 JHQHEPFCSFITQT-UHFFFAOYSA-N 0.000 claims description 4
- XYDLVEIIQDOYDA-UHFFFAOYSA-N 7-bromo-8-methoxy-5-methyl-3-propyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound CC1CN(CCC)CCC2=CC(OC)=C(Br)C=C21 XYDLVEIIQDOYDA-UHFFFAOYSA-N 0.000 claims description 4
- DNLSOPHLIKCIIV-UHFFFAOYSA-N 7-chloro-5-ethyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CCC1CNCCC2=CC=C(Cl)C=C12 DNLSOPHLIKCIIV-UHFFFAOYSA-N 0.000 claims description 4
- OAJYPPWRJRZVRO-UHFFFAOYSA-N 7-chloro-5-ethyl-8-methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CCC1CNCCC2=CC(OC)=C(Cl)C=C12 OAJYPPWRJRZVRO-UHFFFAOYSA-N 0.000 claims description 4
- AELPHXGUKIVCSY-UHFFFAOYSA-N 7-chloro-8-fluoro-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound CC1CNCCC2=CC(F)=C(Cl)C=C12 AELPHXGUKIVCSY-UHFFFAOYSA-N 0.000 claims description 4
- SJJIKXOJEDKQRJ-UHFFFAOYSA-N 7-chloro-8-methoxy-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OC)C(Cl)=C2 SJJIKXOJEDKQRJ-UHFFFAOYSA-N 0.000 claims description 4
- SAJLTUXRPKWFBP-UHFFFAOYSA-N 7-iodo-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepin-8-ol Chemical compound CC1CNCCC2=CC(O)=C(I)C=C12 SAJLTUXRPKWFBP-UHFFFAOYSA-N 0.000 claims description 4
- IIXFGYNBVWNWNL-UHFFFAOYSA-N 7-iodo-8-methoxy-5-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OC)C(I)=C2 IIXFGYNBVWNWNL-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 125000005336 allyloxy group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
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- 230000036186 satiety Effects 0.000 claims description 4
- 230000004584 weight gain Effects 0.000 claims description 4
- WBGUZBYKIJAQIY-UHFFFAOYSA-N 8-methoxy-5-methyl-7-(1,1,2,2,2-pentafluoroethyl)-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OC)C(C(F)(F)C(F)(F)F)=C2 WBGUZBYKIJAQIY-UHFFFAOYSA-N 0.000 claims description 3
- VZPBGKYNLKOIBH-UHFFFAOYSA-N 8-methoxy-5-methyl-7-(trifluoromethyl)-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCC(C)C2=C1C=C(OC)C(C(F)(F)F)=C2 VZPBGKYNLKOIBH-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
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Families Citing this family (84)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8478824B2 (en) * | 2002-02-05 | 2013-07-02 | Portauthority Technologies Inc. | Apparatus and method for controlling unauthorized dissemination of electronic mail |
| SE0200968D0 (sv) * | 2002-03-26 | 2002-03-26 | Lars Baltzer | Novel polypeptide scaffolds and use thereof |
| US6953787B2 (en) * | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
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| US7595311B2 (en) | 2002-05-24 | 2009-09-29 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
| ES2333008T3 (es) | 2002-12-20 | 2010-02-16 | Glaxo Group Limited | Derivados de benzo(d)azepina para el tratamiento de trastornos neurologicos. |
| MXPA05013364A (es) | 2003-06-17 | 2006-03-17 | Arena Pharm Inc | Procedimiento para preparar 3-benzazepinas. |
| AU2004253888B2 (en) * | 2003-06-17 | 2010-11-11 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives useful for the treatment of 5HT2C receptor associated diseases |
| TW200510324A (en) * | 2003-08-11 | 2005-03-16 | Lilly Co Eli | 6-(2,2,2-trifluoroethylamino)-7-chiloro-2, 3, 4, 5-tetrahydro-1h-benzo[d]azepine as a 5-ht2c receptor agonist |
| WO2005042490A1 (en) * | 2003-10-22 | 2005-05-12 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases |
| WO2005042491A1 (en) * | 2003-10-22 | 2005-05-12 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases |
| EP1680127B1 (en) * | 2003-10-23 | 2008-10-15 | F. Hoffmann-La Roche Ag | Benzazepine derivatives as mao-b inhibitors |
| CN102311387A (zh) | 2004-02-25 | 2012-01-11 | 伊莱利利公司 | 作为5-HT2C受体激动剂的6-取代的2,3,4,5-四氢-1H-苯并[d]氮杂䓬 |
| EP2400300A1 (en) | 2004-08-25 | 2011-12-28 | Takeda Pharmaceutical Company Limited | Method of screening preventives/remedies for stress urinary incontinence |
| WO2006028961A2 (en) * | 2004-09-03 | 2006-03-16 | Athersys, Inc. | Tricyclic heteroaryl piperazines, pyrrolidines and azetidines as serotonin receptor modulators |
| US7528175B2 (en) * | 2004-10-08 | 2009-05-05 | Inverseon, Inc. | Method of treating airway diseases with beta-adrenergic inverse agonists |
| WO2006044762A2 (en) * | 2004-10-15 | 2006-04-27 | Bayer Pharmaceuticals Corporation | Tetrahydro-5h-pyrimido[4,5-d]azepine derivatives useful for the treatment of diseases associated with the 5-ht2c receptor |
| JP2008523145A (ja) * | 2004-12-13 | 2008-07-03 | イーライ リリー アンド カンパニー | リポキシゲナーゼ阻害剤としてのスピロ誘導体 |
| PT1838677E (pt) | 2004-12-21 | 2009-11-16 | Arena Pharm Inc | Formas cristalinas do cloridrato de (r)-8-cloro-1-metil- 2,3,4,5-tetra-hidro-1h-3-benzazepina |
| SI1833473T1 (sl) * | 2004-12-23 | 2010-01-29 | Arena Pharm Inc | Sestavki modulatorjev 5HT2C receptorjev in postopki uporabe |
| AU2012201515B2 (en) * | 2004-12-23 | 2015-01-29 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulator compositions and methods of use |
| AP2007004144A0 (en) * | 2005-03-31 | 2007-08-31 | Pfizer Prod Inc | Cyclopentapyridine and tetrahydroquinoline derivatives |
| WO2007025144A1 (en) * | 2005-08-24 | 2007-03-01 | University Of Illinois - Chicago | 5-ht2c receptor agonists as anorectic agents |
| ES2397400T3 (es) | 2005-09-01 | 2013-03-06 | Eli Lilly & Company | 6-arilalquilamino-2,3,4,5-tetrahidro-1H-benzo[D]azepinas como agonistas del receptor 5-HT2C |
| WO2007028132A2 (en) * | 2005-09-01 | 2007-03-08 | Eli Lilly And Company | 6-N-LINKED HETEROCYCLE-SUBSTITUTED 2,3,4,5-TETRAHYDRO-1H-BENZO[d]AZEPINES AS 5-HT2C RECEPTOR AGONISTS |
| CA2619287C (en) * | 2005-09-01 | 2013-10-22 | Eli Lilly And Company | 6-substituted 2,3,4,5-tetrahydro-1h-benzo[d]azepines as 5-ht2c receptor agonists |
| PL1924560T3 (pl) * | 2005-09-01 | 2009-12-31 | Lilly Co Eli | 6 podstawione - 2,3,4,5 - tetrahydro-1h-benzo[d]azepiny jako agoniści receptora 5-ht2c |
| DE102006009004A1 (de) * | 2006-02-23 | 2007-09-06 | Sustech Gmbh & Co. Kg | Multifunktionelle sternförmige Präpolymere, deren Herstellung und Verwendung |
| WO2007120517A2 (en) | 2006-04-03 | 2007-10-25 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates related thereto |
| WO2007132841A1 (ja) | 2006-05-16 | 2007-11-22 | Takeda Pharmaceutical Company Limited | 縮合複素環化合物およびその用途 |
| WO2007140213A1 (en) * | 2006-05-26 | 2007-12-06 | Forest Laboratories Holdings Limited | Pyridoazepine derivatives |
| WO2007149728A2 (en) * | 2006-06-20 | 2007-12-27 | Alcon Research, Ltd. | Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma |
| ATE496894T1 (de) * | 2006-07-14 | 2011-02-15 | Pfizer Prod Inc | Tartratsalz von (7s)-7-ä(5-fluor-2- |
| US8299241B2 (en) * | 2006-12-05 | 2012-10-30 | Arena Pharmaceuticals, Inc. | Processes for preparing (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine and intermediates thereof |
| WO2008071646A1 (en) * | 2006-12-11 | 2008-06-19 | Boehringer Ingelheim International Gmbh | New pyridazine derivatives with mch antagonistic activity and medicaments comprising these compounds |
| US20090143363A1 (en) * | 2007-10-15 | 2009-06-04 | Concert Pharmaceuticals, Inc. | Deuterated lorcaserin |
| JP5520051B2 (ja) | 2007-11-15 | 2014-06-11 | 武田薬品工業株式会社 | 縮合ピリジン誘導体およびその用途 |
| JP5491421B2 (ja) * | 2008-03-04 | 2014-05-14 | アリーナ ファーマシューティカルズ, インコーポレイテッド | 5−ht2cアゴニストである(r)−8−クロロ−1−メチル−2,3,4,5−テトラヒドロ−1h−3−ベンゾアゼピンに関連する中間体の調製のためのプロセス |
| WO2009119534A1 (ja) | 2008-03-26 | 2009-10-01 | 第一三共株式会社 | 新規テトラヒドロイソキノリン誘導体 |
| EP2246331A1 (en) * | 2009-04-24 | 2010-11-03 | Westfälische Wilhelms-Universität Münster | NR2B-selective NMDA-receptor antagonists |
| CN102648170A (zh) | 2009-06-18 | 2012-08-22 | 艾尼纳制药公司 | 制备5-ht2c受体激动剂的方法 |
| JPWO2011071136A1 (ja) | 2009-12-11 | 2013-04-22 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| CA2788416C (en) | 2010-02-04 | 2018-08-14 | The Board Of Trustees Of The University Of Illinois | Highly selective 5-ht(2c) receptor agonists having antagonist activity at the 5-ht(2b) receptor |
| BR112012021231A2 (pt) | 2010-02-26 | 2015-09-08 | Basf Plant Science Co Gmbh | método para acentuar o rendimento em plantas, planta, construto, uso de um construto, método para a produção de uma planta transgênica, partes coletáveis de uma planta, produtos derivados de uma planta, uso de um ácido nucleíco e método para a produção de um produto |
| EP2539364A1 (en) | 2010-02-26 | 2013-01-02 | Novo Nordisk A/S | Peptides for treatment of obesity |
| US20110269744A1 (en) * | 2010-03-12 | 2011-11-03 | Astellas Pharma Inc. | Benzazepine Compound |
| EP2552950A1 (en) | 2010-03-26 | 2013-02-06 | Novo Nordisk A/S | Novel glucagon analogues |
| KR20130112848A (ko) * | 2010-06-02 | 2013-10-14 | 아레나 파마슈티칼스, 인크. | 5-ht2c 수용체 아고니스트의 제조 방법 |
| WO2012030938A1 (en) * | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | Salts of lorcaserin with optically active acids |
| CA2808890A1 (en) | 2010-09-01 | 2012-03-08 | Arena Pharmaceuticals, Inc. | Administration of lorcaserin to individuals with renal impairment |
| JP2013536858A (ja) * | 2010-09-01 | 2013-09-26 | アリーナ ファーマシューティカルズ, インコーポレイテッド | 5−ht2cアゴニストの速く溶解する剤形 |
| SG188361A1 (en) | 2010-09-01 | 2013-04-30 | Arena Pharm Inc | Non-hygroscopic salts of 5-ht2c agonists |
| US20130267500A1 (en) | 2010-09-01 | 2013-10-10 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists in the treatment of disorders ameliorated by reduction of norepinephrine level |
| JP6272695B2 (ja) | 2010-09-01 | 2018-01-31 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 体重管理のために有用な5−ht2cアゴニストの改変放出剤形 |
| US20140031278A1 (en) | 2011-03-28 | 2014-01-30 | Novo Nordisk A/S | Novel Glucagon Analogues |
| AR088161A1 (es) | 2011-09-23 | 2014-05-14 | Novo Nordisk As | Analogos de glucagon |
| CN102895233B (zh) * | 2012-09-04 | 2015-06-24 | 苏州大学 | 苯并氮杂卓类化合物在制备预防或治疗癫痫的药物中的应用 |
| JP2015534563A (ja) | 2012-10-09 | 2015-12-03 | アリーナ ファーマシューティカルズ, インコーポレイテッド | 体重管理の方法 |
| WO2014060575A2 (en) | 2012-10-19 | 2014-04-24 | Medichem S.A. | Process for the enantioselective synthesis of a tetrahydrobenzazepine compound |
| MX362275B (es) | 2013-04-18 | 2019-01-10 | Novo Nordisk As | Co-agonista de peptido similar a glucagon tipo 1 (glp-1) receptor de glucagon de larga duracion, estables para uso medico. |
| EP2999692A1 (en) | 2013-05-20 | 2016-03-30 | LEK Pharmaceuticals d.d. | Novel synthetic processes to 8-chloro-3-benzo[d]azepine via friedel-crafts alkylation of olefin |
| WO2014202765A1 (en) | 2013-06-21 | 2014-12-24 | Lek Pharmaceuticals D.D. | Preparation of chiral 1-methyl-2,3,4,5-1h-benzodiazepines via asymmetric reduction of alpha-substituted styrenes |
| CN105555769A (zh) * | 2013-07-19 | 2016-05-04 | 斯洛文尼亚莱柯制药股份有限公司 | 不需要的对映异构体的外消旋化方法 |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| EP2868656A1 (en) | 2013-11-05 | 2015-05-06 | LEK Pharmaceuticals d.d. | Stabilized amorphous lorcaserin hydrochloride |
| CN104936947B (zh) * | 2013-12-27 | 2017-03-08 | 杭州普晒医药科技有限公司 | 氯卡色林盐及其晶体、其制备方法和用途 |
| WO2015161730A1 (zh) | 2014-04-21 | 2015-10-29 | 杭州普晒医药科技有限公司 | 一种氯卡色林共晶及其制备方法、药物组合物和用途 |
| CN106536547A (zh) | 2014-06-04 | 2017-03-22 | 诺和诺德股份有限公司 | 用于医疗用途的glp‑1/胰高血糖素受体共激动剂 |
| WO2016069875A1 (en) | 2014-10-30 | 2016-05-06 | Arena Pharmaceuticals, Inc. | Compositions and methods for ceasing tobacco smoking |
| US10407381B2 (en) | 2015-01-29 | 2019-09-10 | The Board Of Trustees Of The University Of Illinois | Cyclopropylmethanamines as selective 5-HT(2C) receptor agonists |
| CA3002525A1 (en) * | 2015-07-31 | 2017-02-09 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| DE102015117882A1 (de) * | 2015-10-21 | 2017-04-27 | Mehrdad Ghashghaeinia | Pharmazeutische Zusammensetzung |
| EP3210975A1 (en) | 2016-02-24 | 2017-08-30 | Enantia, S.L. | Cocrystals of lorcaserin |
| JP6725838B2 (ja) * | 2016-09-16 | 2020-07-22 | 富士通クライアントコンピューティング株式会社 | ヒンジ、スタンド装置、及び、電子機器 |
| EP3596107A1 (en) | 2017-03-15 | 2020-01-22 | Novo Nordisk A/S | Bicyclic compounds capable of binding to melanocortin 4 receptor |
| EP3595668B1 (en) | 2017-03-15 | 2021-07-21 | Silverback Therapeutics, Inc. | Benzazepine compounds, conjugates, and uses thereof |
| US20210052600A1 (en) | 2017-12-27 | 2021-02-25 | Takeda Pharmaceutical Company Limited | Therapeutic agents for stress urinary incontinence and incotinence of feces |
| US20210221867A1 (en) | 2018-05-15 | 2021-07-22 | Novo Nordisk A/S | Compounds Capable of Binding to Melanocortin 4 Receptor |
| KR20190132711A (ko) | 2018-05-21 | 2019-11-29 | 주식회사 다림바이오텍 | 비만 예방 또는 치료용 약학 조성물 |
| KR20190133482A (ko) | 2018-05-23 | 2019-12-03 | 동국제약 주식회사 | 흰강낭콩 및 아위버섯 추출물을 함유하는 항비만 또는 체지방 감소용 조성물 |
| WO2020053414A1 (en) | 2018-09-14 | 2020-03-19 | Novo Nordisk A/S | Bicyclic compounds capable of acting as melanocortin 4 receptor agonists |
| EP3860996A4 (en) | 2018-10-02 | 2022-08-31 | Northwestern University | BETA-CARBOLINES AS POSITIVE ALLOSTERIC MODULATORS OF HUMAN SEROTONIN RECEPTOR 2C (5-HT2C) |
| US11179473B2 (en) | 2020-02-21 | 2021-11-23 | Silverback Therapeutics, Inc. | Nectin-4 antibody conjugates and uses thereof |
| CN116209678A (zh) | 2020-07-01 | 2023-06-02 | 安尔士制药公司 | 抗asgr1抗体缀合物及其用途 |
Family Cites Families (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US405495A (en) | 1889-06-18 | Picker-staff connection for looms | ||
| US434607A (en) | 1890-08-19 | Barrel-washing machine | ||
| US372058A (en) | 1887-10-25 | William m | ||
| CH481110A (de) * | 1967-02-17 | 1969-11-15 | Geigy Ag J R | Verfahren zur Herstellung von 1,2,4,5-Tetrahydro-3-azepinen |
| CH498122A (de) | 1968-02-09 | 1970-10-31 | Geigy Ag J R | Verfahren zur Herstellung eines neuen Tetrahydroazepinderivates |
| CH500194A (de) | 1968-02-15 | 1970-12-15 | Ciba Geigy Ag | Verfahren zur Herstellung von Tetrahydroazepinderivaten |
| GB1268243A (en) | 1968-03-11 | 1972-03-22 | Wallace & Tiernan Inc | 0,2,4,5,-tetrahydro-3h,3-benzazepines |
| US4233217A (en) * | 1968-03-11 | 1980-11-11 | Pennwalt Corporation | Substituted 1,2,4,5-tetrahydro-3H, 3 benzazepines |
| FR7736M (enExample) | 1968-09-02 | 1970-03-09 | ||
| US3592523A (en) * | 1969-05-19 | 1971-07-13 | Ncr Co | Angle multiplier apparatus |
| US3716639A (en) * | 1970-03-11 | 1973-02-13 | Ciba Geigy Corp | Anorexigenic tetrahydrobenzazepines |
| US3795683A (en) * | 1970-08-19 | 1974-03-05 | Hoffmann La Roche | 2,3,4,5-tetrahydro-1h-3-benzazepines |
| LU65954A1 (enExample) * | 1972-08-25 | 1974-03-07 | ||
| US4210749A (en) * | 1974-11-12 | 1980-07-01 | Pennwalt Corporation | Substituted 1,2,4,5-tetrahydro-3H,3 benzazepines |
| US4111957A (en) | 1977-02-02 | 1978-09-05 | Smithkline Corporation | Substituted 1-thienyl and furyl-2,3,4,5-tetrahydro-1H-3-benzazepine compounds |
| US4108989A (en) * | 1977-04-01 | 1978-08-22 | Smithkline Corporation | 2,3,4,5-tetrahydro-1h-3-benzazepine-7,8-diones |
| CA1090797A (en) | 1978-06-20 | 1980-12-02 | Kenneth G. Holden | Substituted 1-thienyl and furyl-2,3,4,5-tetrahydro-1h- 3-benzazepine compounds |
| AU515236B2 (en) | 1978-06-26 | 1981-03-26 | Smithkline Corporation | Substituted-1-thienyl and furyl-2,3,4,5-tetrahydro-14-3 benzazepine derivatives |
| ZA792785B (en) | 1978-07-07 | 1980-08-27 | Smithkline Corp | Mercapto substituted-2,3,4,5-tetrahydro-1h-3-benzazepines |
| EP0161350A1 (en) | 1981-11-27 | 1985-11-21 | Smithkline Beckman Corporation | Process for preparing benzazepines |
| FR2525603A1 (fr) | 1982-04-27 | 1983-10-28 | Adir | Benzoazacycloalkyl-spiro-imidazolinines, leur preparation et leur application en therapeutique |
| US4988690A (en) | 1982-06-14 | 1991-01-29 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryloxy-2,3,4,5-tetrahydro-3-benzazepines and anti-depressant use thereof |
| US4541954A (en) | 1984-09-05 | 1985-09-17 | Smithkline Beckman Corporation | Method for preparing 6-chloro-N-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine |
| US4762845A (en) * | 1986-05-21 | 1988-08-09 | Abbott Laboratories | 7-(3-Substituted imino-1-pyrrolidinyl)-quinolone-3-carboxylic acids |
| EP0285287A3 (en) | 1987-03-23 | 1990-08-16 | Smithkline Beecham Corporation | 3-benzazepine compounds for use in treating gastrointestinal motility disorders |
| PH27337A (en) * | 1987-03-27 | 1993-06-08 | Schering Corp | Substituted benzazepines their preparation and pharmaceutical compositions containing them |
| US5015639A (en) * | 1987-03-27 | 1991-05-14 | Schering Corporation | Substituted benzazepines, their preparation and pharmaceutical compositions containing them |
| US5247080A (en) * | 1987-03-27 | 1993-09-21 | Schering Corporation | Substituted benzazepines useful as intermediates for producing pharmaceutically active compounds |
| WO1988007858A1 (en) | 1987-04-09 | 1988-10-20 | Smithkline Beckman Corporation | Sulfinyl and sulfonyl substituted 3-benzazepines |
| US5105639A (en) * | 1989-02-23 | 1992-04-21 | Spiro America Inc. | Apparatus for forming spiral pipe |
| US5422355A (en) * | 1989-06-02 | 1995-06-06 | John Wyeth & Brother, Limited | Composition for treating depression with (N-heteroaryl)alkylamines |
| US5178786A (en) * | 1989-08-04 | 1993-01-12 | The Lubrizol Corporation | Corrosion-inhibiting compositions and functional fluids containing same |
| WO1991019698A1 (en) | 1990-06-15 | 1991-12-26 | Schering Corporation | 8-lower alkyl-5-cycloalkyl or 5-cycloalkenyl substitued benzazepines and pharmaceutical compositions containing them |
| US5275915A (en) * | 1991-06-05 | 1994-01-04 | Dainippon Ink And Chemicals, Inc. | Developer for light-sensitive material |
| PT100602A (pt) | 1991-06-21 | 1993-09-30 | Smithkline Beecham Plc | Uso de derivados de tetra-hidrobenzazepinas, derivados de tetra-hidrobenzazepinas,sua preparacao e composicoes farmaceuticas que os contem |
| EP0558824A1 (en) * | 1992-02-04 | 1993-09-08 | Duphar International Research B.V | Method for the preparation of vicinal aminoalcohols and optically active O-protected derivatives thereof |
| JPH05339263A (ja) | 1992-06-08 | 1993-12-21 | Wakunaga Pharmaceut Co Ltd | ジヒドロピリジン誘導体 |
| JPH06298746A (ja) | 1993-04-19 | 1994-10-25 | Showa Denko Kk | 環状イミド酸エステルの製造法 |
| CA2166100A1 (en) * | 1993-06-23 | 1995-01-05 | Richard A. Glennon | Sigma receptor ligands and the use thereof |
| US5387685A (en) * | 1993-07-16 | 1995-02-07 | American Cyanamid Co | MDR reversal agents |
| GB9322976D0 (en) | 1993-11-08 | 1994-01-05 | Pfizer Ltd | Therapeutic agents |
| DE4419246A1 (de) * | 1994-06-01 | 1995-12-07 | Merckle Gmbh | Heteroarylsubstituierte Pyrrolizinverbindungen und deren Anwendung in der Pharmazie |
| DE4419315A1 (de) * | 1994-06-01 | 1995-12-07 | Merckle Gmbh | Heteropyrrolizinverbindungen und deren Anwendung in der Pharmazie |
| DE4419247A1 (de) * | 1994-06-01 | 1995-12-07 | Merckle Gmbh | Sulfonylierte Pyrrolizincarbonsäureamide und deren Anwendung in der Pharmazie |
| DE4427838A1 (de) | 1994-08-05 | 1996-02-08 | Thomae Gmbh Dr K | Kondensierte Azepinderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| DE4429079A1 (de) | 1994-08-17 | 1996-02-22 | Thomae Gmbh Dr K | Cyclische Harnstoffderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| JPH08134048A (ja) | 1994-11-08 | 1996-05-28 | Sumitomo Chem Co Ltd | オキサゾリン類の製造法 |
| DE19510566A1 (de) * | 1995-03-23 | 1996-09-26 | Kali Chemie Pharma Gmbh | Benzazepin-, Benzoxazepin- und Benzothiazepin-N-essigsäurederivate sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| GB9508622D0 (en) | 1995-04-28 | 1995-06-14 | Pfizer Ltd | Therapeutic agants |
| US5958543A (en) | 1995-07-07 | 1999-09-28 | Stor Media,Inc. | Micro-texturing for sputtered, thin film magnetic media disks utilizing titanium sputtered in the presence of hydrogen to form micro-texturing |
| JPH0930960A (ja) | 1995-07-18 | 1997-02-04 | Takasago Internatl Corp | 真菌感染症治療剤 |
| JPH0987258A (ja) | 1995-09-28 | 1997-03-31 | Sumitomo Chem Co Ltd | オキサゾリン類、その製造方法およびそれを用いる不斉シクロプロパンカルボン酸類の製造方法 |
| CA2190708A1 (en) * | 1995-12-08 | 1997-06-09 | Johannes Aebi | Aminoalkyl substituted benzo-heterocyclic compounds |
| US5892116A (en) | 1996-01-03 | 1999-04-06 | Georgetown University | Gelators |
| US5925651A (en) * | 1996-04-03 | 1999-07-20 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US5691362A (en) * | 1996-06-05 | 1997-11-25 | Schering-Plough Corporation | Substituted benzene-fused hetero- and carbocyclics as nuerokinin antagonists |
| EP0920417A4 (en) | 1996-08-15 | 1999-12-29 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
| AU6290998A (en) | 1997-03-07 | 1998-09-29 | Novo Nordisk A/S | 4,5,6,7-tetrahydro-thieno{3,2-c}pyridine derivatives, their preparation and use |
| AUPP020297A0 (en) | 1997-11-05 | 1997-11-27 | University Of Melbourne, The | A novel receptor, and compounds which bind thereto |
| EP0987235B1 (en) | 1998-08-25 | 2003-03-12 | MERCK PATENT GmbH | Method for the conversion of arenes or alkenes with iodoalkenes, aryl iodides or arenediazonium salts |
| DE60006618T2 (de) * | 1999-08-06 | 2004-09-23 | F. Hoffmann-La Roche Ag | Tetrahydro-benzo(d)azepine und deren Verwendung als metabotrope Glutamatrezeptor-Antagonisten |
| EP1074549B1 (en) | 1999-08-06 | 2003-11-19 | F. Hoffmann-La Roche Ag | Tetrahydro-benzo(d)azepines and their use as antagonists at metabotropic glutamate receptors |
| DE10003708A1 (de) * | 2000-01-28 | 2001-08-02 | Solvent Innovation Gmbh | Neuartige chirale ionische Flüssigkeiten und Verfahren zu ihrer Darstellung in enantiomerenreiner oder enantiomerenangereicherter Form |
| JP4272423B2 (ja) | 2000-11-14 | 2009-06-03 | スミスクライン ビーチャム ピー エル シー | ドーパミンd3受容体のモジュレーターとして有用なテトラヒドロベンズアゼピン誘導体(抗精神病剤) |
| GB0030710D0 (en) | 2000-12-15 | 2001-01-31 | Hoffmann La Roche | Piperazine derivatives |
| JPWO2002074746A1 (ja) | 2001-03-16 | 2004-07-08 | 山之内製薬株式会社 | ベンゾアゼピン誘導体 |
| US6825198B2 (en) | 2001-06-21 | 2004-11-30 | Pfizer Inc | 5-HT receptor ligands and uses thereof |
| MXPA04002785A (es) | 2001-09-24 | 2004-07-29 | Elan Pharm Inc | Aminas sustituidas para tratamiento de enfermedad de alzheimer. |
| AU2003214873A1 (en) | 2002-01-18 | 2003-09-02 | Ceretek Llc | Methods of treating conditions associated with an edg receptor |
| JP3813152B2 (ja) * | 2002-03-12 | 2006-08-23 | メルク エンド カムパニー インコーポレーテッド | 置換アミド類 |
| US6953787B2 (en) * | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
| GB0224557D0 (en) | 2002-10-22 | 2002-11-27 | Glaxo Group Ltd | Novel compounds |
| AU2004253888B2 (en) | 2003-06-17 | 2010-11-11 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives useful for the treatment of 5HT2C receptor associated diseases |
| MXPA05013364A (es) | 2003-06-17 | 2006-03-17 | Arena Pharm Inc | Procedimiento para preparar 3-benzazepinas. |
| WO2005042491A1 (en) | 2003-10-22 | 2005-05-12 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases |
| WO2005042490A1 (en) | 2003-10-22 | 2005-05-12 | Arena Pharmaceuticals, Inc. | Benzazepine derivatives and methods of prophylaxis or treatment of 5ht2c receptor associated diseases |
| JP2008508348A (ja) | 2004-08-02 | 2008-03-21 | ジェンメディカ・セラピューティックス・ソシエダッド・リミターダ | 銅含有アミンオキシダーゼを阻害するための化合物およびその使用 |
| WO2006043710A1 (ja) | 2004-10-19 | 2006-04-27 | Reverse Proteomics Research Institute Co., Ltd. | 創薬標的タンパク質及び標的遺伝子、並びにスクリーニング方法 |
| PT1838677E (pt) | 2004-12-21 | 2009-11-16 | Arena Pharm Inc | Formas cristalinas do cloridrato de (r)-8-cloro-1-metil- 2,3,4,5-tetra-hidro-1h-3-benzazepina |
| SI1833473T1 (sl) | 2004-12-23 | 2010-01-29 | Arena Pharm Inc | Sestavki modulatorjev 5HT2C receptorjev in postopki uporabe |
| WO2007120517A2 (en) | 2006-04-03 | 2007-10-25 | Arena Pharmaceuticals, Inc. | Processes for the preparation of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1h-3-benzazepine and intermediates related thereto |
-
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